Crystal structure and synthesis of benzimidazole substituted acrylonitriles and benzimidazo[1, 2-a]quinolines (original) (raw)
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X-Ray Crystal Structure Analysis of Selected Benzimidazole Derivatives
IntechOpen, 2019
This chapter describes the X-ray crystal structure analysis of selected benzimidazole derivatives, viz. BIP: 2-(1H-benzimidazol-2-yl)phenol, MBMPBI: 1-(4-methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole, DPBI: 1,2-diphenyl-1H-benzimidazole, PBIP: 2-(1-phenyl-1H-benzimidazol-2-yl)phenol, FPPBI: 2-(4-fluorophenyl)-1-phenyl-1H-benzimidazole and NPBIBHS: 2-(naphthalen-1-yl)-1-phenyl-1H-benzimidazole benzene hemisolvate. The BIP molecule is planar, and in the crystal, it is arranged in parallel planes, stabilised by π-π interactions and the hydrogen bonds. In MBMPBI, benzimidazole cores of the two independent (A and B) molecules are planar. Two C▬H…N hydrogen bonds link B molecules only, forming centrosymmetric dimers with R 2 2 (8) ring motifs. In the DPBI molecule, the benzimidazole core is planar: one hydrogen-bond interaction (C▬H…N) and C▬H…π (three) interaction leading to the three-dimensional arrangement. In the PBIP molecule, the benzimidazole is nearly planar. The hydrogen bonds and a π-π stacking interaction are present in the crystal. In the FPPBI molecule, the benzimidazole unit is almost planar. The C▬H…F hydrogen bonds and weak C▬H…π interactions lead to a three-dimensional architecture in the crystal. In NPBIBHS, the naphthalene fragment lies out of the plane about the benzimidazole core unit. The C▬H…N hydrogen bonds and C▬H…π interactions lead to a three-dimensional architecture in the crystal.
Crystal Structure and Pharmacological Importance of Benzimidazoles and Their Derivatives
BJSTR, 2017
Benzimidazoles and their derivatives exhibit a number of important pharmacological properties, such as antihistaminic [1], anti-ulcerative [2], anti allergic [3], and antipyretic [4]. In addition, benzimidazole derivatives are effective against the human cytomegalovirus (HCMV) [5] and are also efficient selective neuropeptide Y Y1 receptor antagonists [6]. We report here in the Crystal structure of 2-(4-(methylthio) phenyl)-1H-benzo[d] imidazole (1) and 2-(4-Methylsulfanylphenyl)-1Hbenzimidazol-3- ium bromide (2).
Different mol-ecular conformations in the crystal structures of three 5-nitro-imidazolyl derivatives
Acta crystallographica. Section E, Crystallographic communications, 2018
The crystal structures of ()-1-methyl-5-nitro-1-imidazole-2-carbaldehyde -benzyl-oxime, CHNO, (I), ()-1-methyl-5-nitro-1-imidazole-2-carb-alde-hyde -(4-fluoro-benz-yl) oxime, CHFNO, (II), and ()-1-methyl-5-nitro-1-imidazole-2-carbaldehyde -(4-bromo-benz-yl) oxime, CHBrNO, (III), are described. The dihedral angle between the ring systems in (I) is 49.66 (5)° and the linking N-C-C=N (m = methyl-ated) bond shows an conformation [torsion angle = 175.00 (15)°]. Compounds (II) and (III) are isostructural [dihedral angle between the aromatic rings = 8.31 (5)° in (II) and 5.34 (15)° in (III)] and differ from (I) in showing a near- conformation for the N-C-C=N linker [torsion angles for (II) and (III) = 17.64 (18) and 8.7 (5)°, respectively], which allows for the occurrence of a short intra-molecular C-H⋯N contact. In the crystal of (I), C-H⋯N hydrogen bonds link the mol-ecules into [010] chains, which are cross-linked by very weak C-H⋯O bonds into (100) sheets. Weak aromatic π-π stacking in...
Synthesis and crystal structure of 1-benzyl-2-(4-benzyloxyphenyl)-5,6-dichloro-1H-benzimidazole
Structural Chemistry, 2008
In this study 1-benzyl-2-(4-benzyloxyphenyl)-5,6-dichloro-1H-benzimidazole, II, was synthesised. Elemental analyses, 1H-NMR, and single-crystal structure determination have been carried out. The benzimidazole ring system is planar as expected. The molecules of II are arranged in rows running parallel to the b-axis with the molecules in adjacent rows inverted.
Crystal Structure of 2-(2,2-Dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile
Journal of Chemical Crystallography, 2011
The crystal structure of 2-(2,2-dibromovinyl)-1methyl-1H-imidazole-4,5-dicarbonitrile (C 8 H 4 Br 2 N 4 , Mr = 315.92) has been determined by single crystal X-ray diffraction analysis. The compound crystallizes in the monoclinic crystal system with space group P2 1 /c and unit cell parameters: a = 15.144 , b = 16.382(3), c = 8.267(1) Å , b = 95.76(2) o and Z = 8. The final reliability index is 0.0297 for 2505 observed reflections. The two molecules of 2-(2,2-dibromovinyl)-4,5-dicyano-1-methylimidazole are localized in independent part of unit cell. The crystal packing is stabilized by C-HÁÁÁN hydrogen bonds and BrÁÁÁN intermolecular interactions.
Journal of Chemical Crystallography, 2004
The synthesis and spectral identification of 1-(4-fluorobenzyl)-2-(4-cyanophenyl)-1Hbenzimidazole-5-carbonitrile (1) have been reported. IR, 1 H NMR, and EI mass spectral analysis were used for its spectral identification. The structure of 1 was confirmed by Xray crystallographic studies. Intramolecular hydrogen bond occurs between the imidazole nitrogen and one of hydrogen of the florobenzene. The crystal packing is governed by C H• • •N intermolecular hydrogen bonds. The molecular structure observed in crystal and the optimised geometries at the HF level by doing semi-empirical and ab initio calculations were compared.